It can be challenging to know how much employer stock to hold as units accumulate in your account. Though cash bonuses continue to be offered, more companies rely on stock as an incentive for you to stick around. So how do you make the most of what you have?

Like ice cream, there are a variety of flavors of stock. It’s important to distinguish what you own, recognize important dates, and understand the short- and long-term tax impacts. Professional advice pays off here and goes beyond what to do in the here and now.  A better question to ask yourself is, “what role does company stock play in my financial house?”

Adding a job description to vested (and future) shares provides clarity to your decisions. Will you liquidate and apply proceeds to recurring expenses or a big-ticket purchase?  Will you let shares increase, with the possibility of a bigger pop in the future? Or are you just too busy to deal with it now?

There is plenty of room for error and opportunity when owning stock in your 20s and 30s. Look no further than all the investors that survived the Tech Bubble twenty-five years ago. As you journey through your 40s, 50s, and beyond, however, it pays to have a more disciplined approach.

Prices will travel up and down for no reason as that is how stocks behave. Sure, fundamentals and management matter, as do earnings. Attempting to forecast a future price and timing a transaction is problematic. Shareholders need more color on their canvas to figure out how employer stock fits in with everything else.

It’s completely natural for employees to anchor around company stock. It can be fun (and addicting) to follow the ups and downs as shares vest over time. Companies reward loyal employees with more units, which in turn sends a signal to everyone. It says, “hang out here, do good work, and you can take part in what we are creating.”

It’s a compelling pitch.

Challenges are created over time as diversification is just not attractive in the near term. Today’s narrative is all about company innovation and growth. In real life planning with clients, loss aversion and the pain of taxes are the real barriers to selling company stock.

Everyone knows “that employee” who sold stock only to watch prices surge in value later. Selling doesn’t feel right as our brains default to “more is better”. FOMO, the fear of missing out, often has employees holding more units than is prudent.

Unfortunately, company stock is ambivalent about who you are and how much you own. It doesn’t matter if you’re in the C-suite or a new employee. Company stock carries no emotion. Accepting this reality is not easy for all investors.

As more of your wealth collects around a particular company, the stakes increase. Sooner or later a decision will need to be made, or will be made for you, based on the value of your shares.

The obvious answer isn’t necessarily the correct one. Selling stock creates another set of questions. It’s just as easy for cash proceeds to settle into your money market account and get comfortable with no purpose. Cash can’t keep pace with the rising cost of living, so what’s a better approach?

What if you created a short-term plan with the shares you’ve accumulated? Before accumulating more or selling, what if you mapped out the next twenty-four months of personal spending at a high level? Accounting for taxes, big ticket purchase(s), investments, and FUN before you decide what to do with your shares.

Then you can go ahead, knowing that your decision aligns with what you want.  Money is personal and there are no right or wrong ways to spend, save, and give what you have. This message gets lost in today’s noise and it’s worth rereading. Your dollars, your choices.

This is planning; because it’s not what you have, it’s what you keep that matters. With employer stock, it makes sense to proactively think through your options before you need to. Conversations yesterday, today, and tomorrow make this possible. This allows investors to minimize long term regret so they can go live their life.